Dimethylamine → HCID 22050369, compound

HRID 1832054Notes

Reaction equation

HRID 1832054 reaction equation
[Br:1][C:2]1[C:3](=[O:28])[N:4]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=2[CH3:27])[CH:22]=O)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[CH3:29][NH:30][CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:47]>>[ClH:47].[Br:1][C:2]1[C:3](=[O:28])[N:4]([C:19]2[CH:20]=[C:21]([CH2:22][N:30]([CH3:31])[CH3:29])[CH:24]=[CH:25][C:26]=2[CH3:27])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 22050686HCID 22050686, compound

Product 1

HCID 22050369HCID 22050369, compoundYield 26%

Procedure

3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzaldehyde (from step 1) (0.50 g, 1.11 mmol) was dissolved in CH2Cl2 (10 ml). N,N-dimethylamine (2.0 M in THF) (1.11 ml, 2.22 mmol) was added. This mixture stirred for at room temperature for 12 hours. Next, sodium tri-acetoxyborohydride (0.47 g, 2.22 mmol) was added and the reaction stirred for two more hours. The reaction was washed with 1 N NaOH (aq.) and then extracted with CH2Cl2. The combined organic extracts were washed with water. The aqueous layer was separated and extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was taken up in diethyl ether. 1M HCl in diethyl ether (5 ml) was added and the precipitate was collected on a filter pad. This precipitate was hygroscopic. The hygroscopic solid was then taken up in hot ethyl acetate. Hexane was added until a precipitate crashed out. The precipitate was collected on a filter pad to yield a white solid (150 mg, 26%). 1H NMR (400 MHz, D2O) δ 7.42 (m, 3H), 7.17 (s, 1H), 6.86 (m, 2H), 6.53 (s, 1H), 5.20 (s, 2H), 4.18 (s, 1H), 2.72 (s, 6H), 1.85 (s, 3H), 1.82 (s, 3H); ES-MS m/z 477 (M+H). ES-HRMS m/z 477.0955 (M+H calcd for C23H24BrF2N2O2 requires 477.0984).

Workup

  1. stirringthe reaction stirred for two more hours
  2. washThe reaction was washed with 1 N NaOH (aq.)
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with water
  5. customThe aqueous layer was separated
  6. extractionextracted with CH2Cl2
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. addition1M HCl in diethyl ether (5 ml) was added
  11. customthe precipitate was collected on a filter pad
  12. additionHexane was added until a precipitate
  13. customThe precipitate was collected on a filter pad

Sources & evidence

ORD record
ord-4e158cc0824849a68345699d0453d45f
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

Loading…